AU765212B2 - 1-arenesulfonyl-2-aryl-pyrrolidine and piperidine derivatives for the treatment of CNS disorders - Google Patents

1-arenesulfonyl-2-aryl-pyrrolidine and piperidine derivatives for the treatment of CNS disorders Download PDF

Info

Publication number: AU765212B2
Authority: AU; Australia
Prior art keywords: pyrrolidine; phenyl; toluene; sulfonyl; fluoro
Prior art date: 1999-03-25
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.): Ceased

Application number

AU32915/00A

Other languages

English (en)

Other versions

AU3291500A (en

Inventor

Vincent Mutel

Eric Vieira

Jurgen Wichmann

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

F Hoffmann La Roche AG

Original Assignee

F Hoffmann La Roche AG

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1999-03-25

Filing date

2000-03-18

Publication date

2003-09-11

2000-03-18 Application filed by F Hoffmann La Roche AG filed Critical F Hoffmann La Roche AG

2000-10-16 Publication of AU3291500A publication Critical patent/AU3291500A/en

2003-09-11 Application granted granted Critical

2003-09-11 Publication of AU765212B2 publication Critical patent/AU765212B2/en

2020-03-18 Anticipated expiration legal-status Critical

Status Ceased legal-status Critical Current

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RWRDLPDLKQPQOW-UHFFFAOYSA-N tetrahydropyrrole Substances C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 title claims description 74
150000003053 piperidines Chemical class 0.000 title description 3
208000015114 central nervous system disease Diseases 0.000 title 1
150000001875 compounds Chemical class 0.000 claims description 155
150000003839 salts Chemical class 0.000 claims description 33
-1 -C 7 )-alkyl Chemical group 0.000 claims description 27
239000003814 drug Substances 0.000 claims description 21
238000000034 method Methods 0.000 claims description 18
238000004519 manufacturing process Methods 0.000 claims description 15
208000002193 Pain Diseases 0.000 claims description 14
208000027089 Parkinsonian disease Diseases 0.000 claims description 14
206010034010 Parkinsonism Diseases 0.000 claims description 14
230000001154 acute effect Effects 0.000 claims description 14
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 11
WHUUTDBJXJRKMK-VKHMYHEASA-N L-glutamic acid Chemical compound OC(=O)[C@@H](N)CCC(O)=O WHUUTDBJXJRKMK-VKHMYHEASA-N 0.000 claims description 10
230000006870 function Effects 0.000 claims description 10
230000001684 chronic effect Effects 0.000 claims description 9
230000002265 prevention Effects 0.000 claims description 9
WRLSSXDFVXDSKD-UHFFFAOYSA-N 2-(4-methylphenyl)-1-(4-methylphenyl)sulfonylpyrrolidine Chemical compound C1=CC(C)=CC=C1C1N(S(=O)(=O)C=2C=CC(C)=CC=2)CCC1 WRLSSXDFVXDSKD-UHFFFAOYSA-N 0.000 claims description 8
208000024827 Alzheimer disease Diseases 0.000 claims description 8
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206010002026 amyotrophic lateral sclerosis Diseases 0.000 claims description 8
229930195712 glutamate Natural products 0.000 claims description 8
229910052739 hydrogen Inorganic materials 0.000 claims description 8
239000001257 hydrogen Substances 0.000 claims description 8
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 8
230000008569 process Effects 0.000 claims description 8
OOVSRCPGHGCJAM-UHFFFAOYSA-N 1-(4-methylphenyl)sulfonyl-2-phenylpyrrolidine Chemical compound C1=CC(C)=CC=C1S(=O)(=O)N1C(C=2C=CC=CC=2)CCC1 OOVSRCPGHGCJAM-UHFFFAOYSA-N 0.000 claims description 7
208000030507 AIDS Diseases 0.000 claims description 7
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208000020564 Eye injury Diseases 0.000 claims description 7
206010019196 Head injury Diseases 0.000 claims description 7
208000010496 Heart Arrest Diseases 0.000 claims description 7
208000023105 Huntington disease Diseases 0.000 claims description 7
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 7
208000013016 Hypoglycemia Diseases 0.000 claims description 7
206010021143 Hypoxia Diseases 0.000 claims description 7
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206010047700 Vomiting Diseases 0.000 claims description 7
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ZLRBSTSPRRCHES-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-1-(4-methylphenyl)sulfonylpyrrolidine Chemical compound C1=C(OC)C(OC)=CC=C1C1N(S(=O)(=O)C=2C=CC(C)=CC=2)CCC1 ZLRBSTSPRRCHES-UHFFFAOYSA-N 0.000 claims description 6
150000002367 halogens Chemical class 0.000 claims description 6
208000020431 spinal cord injury Diseases 0.000 claims description 6
125000001424 substituent group Chemical group 0.000 claims description 6
JZWZRZYTVFZHIA-UHFFFAOYSA-N 3-[1-(4-methylphenyl)sulfonylpyrrolidin-2-yl]pyridine Chemical compound C1=CC(C)=CC=C1S(=O)(=O)N1C(C=2C=NC=CC=2)CCC1 JZWZRZYTVFZHIA-UHFFFAOYSA-N 0.000 claims description 5
125000004093 cyano group Chemical group *C#N 0.000 claims description 5
230000007812 deficiency Effects 0.000 claims description 5
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 5
YFHJJRUCGDZFIL-MAUKXSAKSA-N (2r,3s)-3-methyl-1-(4-methylphenyl)sulfonyl-2-phenylpyrrolidine Chemical compound C1([C@@H]2N(CC[C@@H]2C)S(=O)(=O)C=2C=CC(C)=CC=2)=CC=CC=C1 YFHJJRUCGDZFIL-MAUKXSAKSA-N 0.000 claims description 4
125000000524 functional group Chemical group 0.000 claims description 4
125000002541 furyl group Chemical group 0.000 claims description 4
239000000546 pharmaceutical excipient Substances 0.000 claims description 4
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QJZKEMXDPJECSV-UHFFFAOYSA-N 1-(4-methylphenyl)sulfonyl-2-thiophen-2-ylpyrrolidine Chemical compound C1=CC(C)=CC=C1S(=O)(=O)N1C(C=2SC=CC=2)CCC1 QJZKEMXDPJECSV-UHFFFAOYSA-N 0.000 claims description 3
125000005843 halogen group Chemical group 0.000 claims description 3
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
UNWYOYFLGMANQV-UHFFFAOYSA-N 1-(4-chlorophenyl)sulfonyl-2-(4-fluorophenyl)pyrrolidine Chemical compound C1=CC(F)=CC=C1C1N(S(=O)(=O)C=2C=CC(Cl)=CC=2)CCC1 UNWYOYFLGMANQV-UHFFFAOYSA-N 0.000 claims description 2
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WMCBPITWUUHVJB-UHFFFAOYSA-N 1-(4-chlorophenyl)sulfonyl-2-thiophen-2-ylpyrrolidine Chemical compound C1=CC(Cl)=CC=C1S(=O)(=O)N1C(C=2SC=CC=2)CCC1 WMCBPITWUUHVJB-UHFFFAOYSA-N 0.000 claims description 2
RMZAYRXUTNJSDZ-UHFFFAOYSA-N 1-(4-methylphenyl)sulfonyl-2-thiophen-3-ylpyrrolidine Chemical compound C1=CC(C)=CC=C1S(=O)(=O)N1C(C2=CSC=C2)CCC1 RMZAYRXUTNJSDZ-UHFFFAOYSA-N 0.000 claims description 2
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QNROCOCNCGNWCU-UHFFFAOYSA-N 2-(3-methylphenyl)-1-(4-methylphenyl)sulfonylpyrrolidine Chemical compound C1=CC(C)=CC=C1S(=O)(=O)N1C(C=2C=C(C)C=CC=2)CCC1 QNROCOCNCGNWCU-UHFFFAOYSA-N 0.000 claims description 2
YKEZZMRBHZDMST-UHFFFAOYSA-N 2-(4-fluorophenyl)-1-(2-methylphenyl)sulfonylpyrrolidine Chemical compound CC1=CC=CC=C1S(=O)(=O)N1C(C=2C=CC(F)=CC=2)CCC1 YKEZZMRBHZDMST-UHFFFAOYSA-N 0.000 claims description 2
MSYGBWPPRVPMSJ-UHFFFAOYSA-N 2-(4-fluorophenyl)-1-(4-fluorophenyl)sulfonylpyrrolidine Chemical compound C1=CC(F)=CC=C1C1N(S(=O)(=O)C=2C=CC(F)=CC=2)CCC1 MSYGBWPPRVPMSJ-UHFFFAOYSA-N 0.000 claims description 2
DAEHFYNGSSBGSS-UHFFFAOYSA-N 2-(4-fluorophenyl)-1-(4-methylphenyl)sulfonylpyrrolidine Chemical compound C1=CC(C)=CC=C1S(=O)(=O)N1C(C=2C=CC(F)=CC=2)CCC1 DAEHFYNGSSBGSS-UHFFFAOYSA-N 0.000 claims description 2
125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 claims description 2
125000001624 naphthyl group Chemical group 0.000 claims description 2
125000006701 (C1-C7) alkyl group Chemical group 0.000 claims 1
XZVSIWOHBXELCZ-UHFFFAOYSA-N 1-(4-ethylphenyl)sulfonyl-2-(4-fluorophenyl)pyrrolidine Chemical compound C1=CC(CC)=CC=C1S(=O)(=O)N1C(C=2C=CC(F)=CC=2)CCC1 XZVSIWOHBXELCZ-UHFFFAOYSA-N 0.000 claims 1
OBQGFKZKOZCQEZ-UHFFFAOYSA-N 1-(benzenesulfonyl)-2-(4-chlorophenyl)pyrrolidine Chemical compound C1=CC(Cl)=CC=C1C1N(S(=O)(=O)C=2C=CC=CC=2)CCC1 OBQGFKZKOZCQEZ-UHFFFAOYSA-N 0.000 claims 1
LCBAARXFUPCPHC-UHFFFAOYSA-N 2-(3,4-difluorophenyl)-1-(4-methylphenyl)sulfonylpyrrolidine Chemical compound C1=CC(C)=CC=C1S(=O)(=O)N1C(C=2C=C(F)C(F)=CC=2)CCC1 LCBAARXFUPCPHC-UHFFFAOYSA-N 0.000 claims 1
DJJHVXPLTOQHNQ-UHFFFAOYSA-N 2-(3-chlorophenyl)-1-(4-methylphenyl)sulfonylpyrrolidine Chemical compound C1=CC(C)=CC=C1S(=O)(=O)N1C(C=2C=C(Cl)C=CC=2)CCC1 DJJHVXPLTOQHNQ-UHFFFAOYSA-N 0.000 claims 1
RQFMCSPTHHBBQD-UHFFFAOYSA-N 2-(4-chloro-3-methylphenyl)-1-(4-methylphenyl)sulfonylpyrrolidine Chemical compound C1=CC(C)=CC=C1S(=O)(=O)N1C(C=2C=C(C)C(Cl)=CC=2)CCC1 RQFMCSPTHHBBQD-UHFFFAOYSA-N 0.000 claims 1
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MYKUKUCHPMASKF-UHFFFAOYSA-N nornicotine Chemical compound C1CCNC1C1=CC=CN=C1 MYKUKUCHPMASKF-UHFFFAOYSA-N 0.000 description 1
QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
239000010502 orange oil Substances 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
235000005985 organic acids Nutrition 0.000 description 1
230000003204 osmotic effect Effects 0.000 description 1
125000004430 oxygen atom Chemical group O* 0.000 description 1
229920002866 paraformaldehyde Polymers 0.000 description 1
238000007911 parenteral administration Methods 0.000 description 1
239000002245 particle Substances 0.000 description 1
230000035790 physiological processes and functions Effects 0.000 description 1
239000011591 potassium Substances 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
NNFCIKHAZHQZJG-UHFFFAOYSA-N potassium cyanide Chemical compound [K+].N#[C-] NNFCIKHAZHQZJG-UHFFFAOYSA-N 0.000 description 1
238000002360 preparation method Methods 0.000 description 1
239000003755 preservative agent Substances 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
239000000018 receptor agonist Substances 0.000 description 1
229940044601 receptor agonist Drugs 0.000 description 1
239000002464 receptor antagonist Substances 0.000 description 1
229940044551 receptor antagonist Drugs 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
229930195734 saturated hydrocarbon Natural products 0.000 description 1
229930000044 secondary metabolite Natural products 0.000 description 1
210000002265 sensory receptor cell Anatomy 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
210000000278 spinal cord Anatomy 0.000 description 1
239000003381 stabilizer Substances 0.000 description 1
239000008117 stearic acid Substances 0.000 description 1
238000003756 stirring Methods 0.000 description 1
238000006467 substitution reaction Methods 0.000 description 1
239000005720 sucrose Substances 0.000 description 1
YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 1
239000001117 sulphuric acid Substances 0.000 description 1
235000011149 sulphuric acid Nutrition 0.000 description 1
239000000725 suspension Substances 0.000 description 1
239000003765 sweetening agent Substances 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
239000006188 syrup Substances 0.000 description 1
235000020357 syrup Nutrition 0.000 description 1
239000011975 tartaric acid Substances 0.000 description 1
235000002906 tartaric acid Nutrition 0.000 description 1
LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical class C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 1
230000001225 therapeutic effect Effects 0.000 description 1
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
238000005303 weighing Methods 0.000 description 1
239000000080 wetting agent Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/06—Antimigraine agents
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/14—Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/18—Antipsychotics, i.e. neuroleptics; Drugs for mania or schizophrenia
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/24—Antidepressants
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/30—Drugs for disorders of the nervous system for treating abuse or dependence
- A61P25/34—Tobacco-abuse
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/30—Drugs for disorders of the nervous system for treating abuse or dependence
- A61P25/36—Opioid-abuse
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/46—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with hetero atoms directly attached to the ring nitrogen atom
- C07D207/48—Sulfur atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/04—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond

Landscapes

Health & Medical Sciences (AREA)
Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
Veterinary Medicine (AREA)
Animal Behavior & Ethology (AREA)
Public Health (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
General Health & Medical Sciences (AREA)
Pharmacology & Pharmacy (AREA)
Life Sciences & Earth Sciences (AREA)
Neurosurgery (AREA)
Biomedical Technology (AREA)
Neurology (AREA)
Psychiatry (AREA)
Addiction (AREA)
Pain & Pain Management (AREA)
Diabetes (AREA)
Endocrinology (AREA)
Urology & Nephrology (AREA)
Hematology (AREA)
Hospice & Palliative Care (AREA)
Vascular Medicine (AREA)
Heart & Thoracic Surgery (AREA)
Emergency Medicine (AREA)
Obesity (AREA)
Cardiology (AREA)
Psychology (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Plural Heterocyclic Compounds (AREA)
Hydrogenated Pyridines (AREA)
Pyrrole Compounds (AREA)

AU32915/00A 1999-03-25 2000-03-18 1-arenesulfonyl-2-aryl-pyrrolidine and piperidine derivatives for the treatment of CNS disorders Ceased AU765212B2 (en)

Applications Claiming Priority (3)

Application Number	Priority Date	Filing Date	Title
EP99106004		1999-03-25
EP99106004		1999-03-25
PCT/EP2000/002431 WO2000058285A1 (en)	1999-03-25	2000-03-18	1-arenesulfonyl-2-aryl-pyrrolidine and piperidine derivatives for the treatment of cns disorders

Publications (2)

Publication Number	Publication Date
AU3291500A AU3291500A (en)	2000-10-16
AU765212B2 true AU765212B2 (en)	2003-09-11

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ID=8237852

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
AU32915/00A Ceased AU765212B2 (en)	1999-03-25	2000-03-18	1-arenesulfonyl-2-aryl-pyrrolidine and piperidine derivatives for the treatment of CNS disorders

Country Status (34)

Country	Link
US (1)	US6284785B1 (es)
EP (1)	EP1165510B1 (es)
JP (1)	JP3590589B2 (es)
KR (1)	KR100452648B1 (es)
CN (1)	CN1150165C (es)
AR (1)	AR028817A1 (es)
AT (1)	ATE305451T1 (es)
AU (1)	AU765212B2 (es)
BR (1)	BR0009278A (es)
CA (1)	CA2368418C (es)
CO (1)	CO5050296A1 (es)
CZ (1)	CZ20013402A3 (es)
DE (1)	DE60022867T2 (es)
DK (1)	DK1165510T3 (es)
ES (1)	ES2249249T3 (es)
HK (1)	HK1044944B (es)
HR (1)	HRP20010682A2 (es)
HU (1)	HUP0200284A3 (es)
IL (1)	IL145301A0 (es)
JO (1)	JO2274B1 (es)
MA (1)	MA26779A1 (es)
MX (1)	MXPA01009623A (es)
MY (1)	MY125295A (es)
NO (1)	NO319948B1 (es)
NZ (1)	NZ514037A (es)
PE (1)	PE20001583A1 (es)
PL (1)	PL204436B1 (es)
RU (1)	RU2248350C2 (es)
SI (1)	SI1165510T1 (es)
TR (1)	TR200102789T2 (es)
TW (1)	TW575561B (es)
WO (1)	WO2000058285A1 (es)
YU (1)	YU67601A (es)
ZA (1)	ZA200107689B (es)

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US20040267010A1 (en) *	2001-02-02	2004-12-30	Forbes Ian Thomson	Sulfonamide compounds, their preparation and use
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AU2005215136A1 (en) *	2004-02-20	2005-09-01	Novartis Ag	DPP-IV inhibitors for treating neurodegeneration and cognitive disorders
JP2007538106A (ja) *	2004-05-20	2007-12-27	イーランファーマスーティカルズ、インコーポレイテッド	γセクレターゼのＮ−環式スルホンアミド阻害剤
WO2006036024A1 (ja)	2004-09-30	2006-04-06	Takeda Pharmaceutical Company Limited	プロトンポンプ阻害薬
EP2258358A3 (en)	2005-08-26	2011-09-07	Braincells, Inc.	Neurogenesis with acetylcholinesterase inhibitor
EP2275096A3 (en)	2005-08-26	2011-07-13	Braincells, Inc.	Neurogenesis via modulation of the muscarinic receptors
DK1919865T3 (da)	2005-08-30	2011-05-23	Takeda Pharmaceutical	1-Heterocyclylsulfonyl, 2-aminomethyl, 5-(hetero-)aryl-substituerede 1-h-pyrrolderivater som syresekretionsinhibitorer
AU2006304787A1 (en)	2005-10-21	2007-04-26	Braincells, Inc.	Modulation of neurogenesis by PDE inhibition
CA2625210A1 (en)	2005-10-31	2007-05-10	Braincells, Inc.	Gaba receptor mediated modulation of neurogenesis
US20100216734A1 (en)	2006-03-08	2010-08-26	Braincells, Inc.	Modulation of neurogenesis by nootropic agents
AU2007249399A1 (en)	2006-05-09	2007-11-22	Braincells, Inc.	Neurogenesis by modulating angiotensin
AU2007249435A1 (en)	2006-05-09	2007-11-22	Braincells, Inc.	5 HT receptor mediated neurogenesis
BRPI0716604A2 (pt)	2006-09-08	2013-04-09	Braincells Inc	combinaÇÕes contendo um derivado de 4-acilaminopiridina
US20100184806A1 (en)	2006-09-19	2010-07-22	Braincells, Inc.	Modulation of neurogenesis by ppar agents
US8933105B2 (en)	2007-02-28	2015-01-13	Takeda Pharmaceutical Company Limited	Pyrrole compounds
EP2318390B1 (en)	2008-08-27	2013-05-01	Takeda Pharmaceutical Company Limited	Pyrrole compounds
US20100216805A1 (en)	2009-02-25	2010-08-26	Braincells, Inc.	Modulation of neurogenesis using d-cycloserine combinations
GB201702221D0 (en)	2017-02-10	2017-03-29	Univ Of Sussex	Compounds
US10603313B2 (en)	2017-07-31	2020-03-31	Chiromics, LLC	Allosteric modulators of the mu opioid receptor
GB201803340D0 (en)	2018-03-01	2018-04-18	Univ Of Sussex	Compounds

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GB9612884D0 (en) *	1996-06-20	1996-08-21	Smithkline Beecham Plc	Novel compounds

2000
- 2000-03-13 TW TW89104504A patent/TW575561B/zh active
- 2000-03-18 PL PL350679A patent/PL204436B1/pl not_active IP Right Cessation
- 2000-03-18 DE DE60022867T patent/DE60022867T2/de not_active Expired - Lifetime
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- 2000-03-18 MX MXPA01009623A patent/MXPA01009623A/es active IP Right Grant
- 2000-03-18 AT AT00910863T patent/ATE305451T1/de active
- 2000-03-18 KR KR10-2001-7012227A patent/KR100452648B1/ko not_active Expired - Fee Related
- 2000-03-18 CN CNB008055300A patent/CN1150165C/zh not_active Expired - Fee Related
- 2000-03-18 AU AU32915/00A patent/AU765212B2/en not_active Ceased
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- 2000-03-18 HK HK02106320.6A patent/HK1044944B/zh not_active IP Right Cessation
- 2000-03-18 JP JP2000607988A patent/JP3590589B2/ja not_active Expired - Fee Related
- 2000-03-18 HR HR20010682A patent/HRP20010682A2/hr not_active Application Discontinuation
- 2000-03-18 YU YU67601A patent/YU67601A/sh unknown
- 2000-03-18 BR BR0009278-9A patent/BR0009278A/pt active Search and Examination
- 2000-03-18 EP EP00910863A patent/EP1165510B1/en not_active Expired - Lifetime
- 2000-03-18 HU HU0200284A patent/HUP0200284A3/hu unknown
- 2000-03-18 SI SI200030753T patent/SI1165510T1/sl unknown
- 2000-03-18 CZ CZ20013402A patent/CZ20013402A3/cs unknown
- 2000-03-18 RU RU2001126570/04A patent/RU2248350C2/ru not_active IP Right Cessation
- 2000-03-18 DK DK00910863T patent/DK1165510T3/da active
- 2000-03-20 PE PE2000000241A patent/PE20001583A1/es not_active Application Discontinuation
- 2000-03-22 CO CO00020380A patent/CO5050296A1/es unknown
- 2000-03-23 AR ARP000101297A patent/AR028817A1/es unknown
- 2000-03-23 JO JO200025A patent/JO2274B1/en active
- 2000-03-23 MY MYPI20001145A patent/MY125295A/en unknown
- 2000-03-24 US US09/534,380 patent/US6284785B1/en not_active Expired - Fee Related
2001
- 2001-09-18 ZA ZA200107689A patent/ZA200107689B/xx unknown
- 2001-09-24 NO NO20014617A patent/NO319948B1/no unknown
- 2001-09-25 MA MA26339A patent/MA26779A1/fr unknown
2004
- 2004-01-30 NZ NZ514037A patent/NZ514037A/xx unknown

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TETRAHEDRON LETTERS, 1993, 34, PP 6205-65208 *

Also Published As

Publication number	Publication date
WO2000058285A1 (en)	2000-10-05
CN1150165C (zh)	2004-05-19
RU2248350C2 (ru)	2005-03-20
YU67601A (sh)	2004-09-03
JO2274B1 (en)	2005-04-07
IL145301A0 (en)	2002-06-30
EP1165510A1 (en)	2002-01-02
NZ514037A (en)	2004-01-30
DE60022867T2 (de)	2006-06-22
NO319948B1 (no)	2005-10-03
PL204436B1 (pl)	2010-01-29
PL350679A1 (en)	2003-01-27
ZA200107689B (en)	2002-12-18
AR028817A1 (es)	2003-05-28
MA26779A1 (fr)	2004-12-20
EP1165510B1 (en)	2005-09-28
CA2368418A1 (en)	2000-10-05
CN1345311A (zh)	2002-04-17
ATE305451T1 (de)	2005-10-15
PE20001583A1 (es)	2001-01-15
HUP0200284A3 (en)	2003-04-28
MY125295A (en)	2006-07-31
HUP0200284A2 (en)	2002-06-29
HRP20010682A2 (en)	2002-10-31
HK1044944B (zh)	2004-10-21
SI1165510T1 (sl)	2005-12-31
DE60022867D1 (de)	2006-02-09
CA2368418C (en)	2009-03-10
TW575561B (en)	2004-02-11
DK1165510T3 (da)	2006-02-06
NO20014617L (no)	2001-09-24
CZ20013402A3 (cs)	2002-03-13
CO5050296A1 (es)	2001-06-27
MXPA01009623A (es)	2002-05-06
US6284785B1 (en)	2001-09-04
BR0009278A (pt)	2001-12-26
JP2002540191A (ja)	2002-11-26
KR20010108403A (ko)	2001-12-07
AU3291500A (en)	2000-10-16
TR200102789T2 (tr)	2002-04-22
ES2249249T3 (es)	2006-04-01
KR100452648B1 (ko)	2004-10-12
NO20014617D0 (no)	2001-09-24
HK1044944A1 (en)	2002-11-08
JP3590589B2 (ja)	2004-11-17

Publication	Publication Date	Title
AU765212B2 (en)	2003-09-11	1-arenesulfonyl-2-aryl-pyrrolidine and piperidine derivatives for the treatment of CNS disorders
RU2052457C1 (ru)	1996-01-20	Производные индола
DE60312998T2 (de)	2007-12-13	1-amido-4-phenyl-4-benzyloxymethyl-piperidin derivative und verwandte verbindungen als neurokinin-1 (nk-1) antagonsisten zur behandlung von erbrechen, depressionen, angstzustände und husten
EP2205565B1 (en)	2013-04-17	1,3-disubstituted-4-phenyl-1 h-pyridin-2-ones
EP1171423B1 (en)	2005-01-12	Carbamic acid derivatives and their use as metabotropic glutamate receptor ligands
PL203071B1 (pl)	2009-08-31	Pochodne piperydyny, ich zastosowania, zawierająca je kompozycja farmaceutyczna oraz sposób ich wytwarzania
CA2084542A1 (en)	1993-06-10	Novel azaheterocyclylmethyl-chromans
IL125358A (en)	2002-09-12	History - 5,2 Diphenyl 5H-Thiazole [3, -2a] Pyrimidine-6-alkanone, their preparation and pharmaceutical preparations containing them
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